Crosslinked pi-conjugated heteroacene compound for organic electroluminescence device and organic electroluminescence device using the same

Abstract

Provided are an organic electroluminescence device, which: shows high luminous efficiency; is free of any pixel defect; and has a long lifetime, and a material for an organic electroluminescence device for realizing the device. The material for an organic electroluminescence device is a compound of a specific structure having a π-conjugated heteroacene skeleton crosslinked with a carbon atom, nitrogen atom, or oxygen atom. The organic electroluminescence device has one or more organic thin film layers including a light emitting layer between a cathode and an anode, and at least one layer of the organic thin film layers contains the material for an organic electroluminescence device.

1. A material for an organic electroluminescence device represented by one of formulae (1) and (2): 
       
         
           
           
               
               
           
         
       
       wherein:
 X 1  and X 2  each independently represent O, N—R 1 , or CR 2 R 3 , provided that a case where both X 1  and X 2  represent CR 2 R 3  is excluded; 
 R 1 , R 2 , and R 3  each independently represent an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having a ring formed of 3 to 24 atoms, provided that, when both X 1  and X 2  represent N—R 1 , at least one R 1  represents a residue of dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, dihydroacridine or N-methylbenzimidazole, wherein the residue is optionally substituted by a substituent selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having a ring formed of 3 to 40 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkoxy group having a ring formed of 3 to 10 carbon atoms, an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an amino group substituted with an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an ester group having an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an ester group having an alkyl group having 1 to 6 carbon atoms, cyano group, nitro group, and halogen atom; 
 n represents 2, 3, or 4, and the material represented by the formula (2) comprises a dimer using L 3  as a linking group for n=2, a trimer using L 3  as a linking group for n=3, or a tetramer using L 3  as a linking group for n=4; 
 L 1  represents a single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, monovalent or divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalent or divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with a benzene ring a through a carbon-carbon bond; 
 L 2  represents a single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, monovalent or divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalent or divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with a benzene ring c through a carbon-carbon bond; 
 when n represents 2, L 3  represents a single bond, an alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond, when n represents 3, L 3  represents a trivalent alkane having 1 to 20 carbon atoms, a substituted or unsubstituted, trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, a substituted or unsubstituted, trivalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalent aromatic heterocyclic group which has 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond, or when n represents 4, L 3  represents a tetravalent alkane having 1 to 20 carbon atoms, a substituted or unsubstituted, tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, a silicon atom, a substituted or unsubstituted, tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, tetravalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond; 
 A l  represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or an aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with L 1  through a carbon-carbon bond, provided that, when L 1  represents an alkyl or alkylene group having 1 to 20 carbon atoms, a case where A 1  represents a hydrogen atom is excluded; 
 A 2  represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or an aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with L 2  through a carbon-carbon bond, provided that, when L 2  represents an alkyl or alkylene group having 1 to 20 carbon atoms, a case where A 2  represents a hydrogen atom is excluded, and, when X 1  and X 2  each represent O or CR 2 R 3  and both L 1  and L 2  represent single bonds, a case where A l  and A 2  simultaneously represent hydrogen atoms is excluded; 
 the substituent of A 1  and A 2  is selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having a ring formed of 3 to 40 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a cycloalkoxy group having a ring formed of 3 to 10 carbon atoms, an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an aromatic heterocyclic group having a ring formed of 3 to 40 atoms, an amino group substituted with an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an ester group having an aromatic hydrocarbon group having a ring formed of 6 to 40 carbon atoms, an ester group having an alkyl group having 1 to 6 carbon atoms, cyano group, nitro group, and halogen atom; 
 Y 1 , Y 2 , and Y 3  each represent an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring a, b, or c through a carbon-carbon bond, a number of each of Y 1  and Y 3  is 0, 1, 2, or 3, and a number of Y 2  is 0, 1, or 2; and 
 A 1 , A 2 , L 1 , L 2 , and L 3  are each free of any carbonyl group. 
 
     
     
       2. The material for an organic electroluminescence device according to  claim 1 , wherein the material for an organic electroluminescence device is represented by any one of formulae (3) to (10): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , n, L 1 , L 2 , L 3 , A 1 , A 2 , Y 1 , Y 2 , and Y 3  are as defined in  claim 1 . 
     
     
       3. An organic electroluminescence device comprising one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one layer of the organic thin film layers comprises the material for an organic electroluminescence device according to  claim 1 . 
     
     
       4. The organic electroluminescence device according to  claim 3 , wherein the light emitting layer comprises the material for an organic electroluminescence device as a host material. 
     
     
       5. The organic electroluminescence device according to  claim 4 , wherein the light emitting layer further comprises a phosphorescent material. 
     
     
       6. The organic electroluminescence device according to  claim 5 , wherein the phosphorescent material comprises an orthometalated complex of an iridium (Ir), osmium (Os), or platinum (Pt) metal. 
     
     
       7. The organic electroluminescence device according to  claim 4 , further comprising an electron injecting layer between the light emitting layer and the cathode, wherein the electron injecting layer comprises a nitrogen-containing ring derivative. 
     
     
       8. The organic electroluminescence device according to  claim 3 , further comprising a hole transporting layer between the light emitting layer and the anode, wherein the hole transporting layer comprises the material for an organic electroluminescence device. 
     
     
       9. The organic electroluminescence device according to  claim 3 , further comprising a reducing dopant at an interfacial region between the cathode and the organic thin film layers. 
     
     
       10. The organic electroluminescence device according to  claim 3 , further comprising an electron transporting layer between the light emitting layer and the cathode, wherein the electron transporting layer comprises the material for an organic electroluminescence device. 
     
     
       11. The organic electroluminescence device according to  claim 10 , wherein the light emitting layer comprises a host material and a phosphorescent material, and the phosphorescent material comprises an orthometalated complex of an iridium (Ir), osmium (Os), or platinum (Pt) metal. 
     
     
       12. The organic electroluminescence device according to  claim 11 , wherein host material comprises a material for an organic electroluminescence device represented by any one of formulae (15) to (18): 
       
         
           
           
               
               
           
         
       
       wherein:
 X 3 , X 4 , X 5 , and X 6  each independently represent O, S, N—R 1 , or CR 2 R 3 ; 
 R 1 , R 2 , and R 3  each independently represent an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having a ring formed of 3 to 24 atoms, provided that, when both X 3  and X 4 , or both X 5  and X 6 , represent N—R 1 , at least one R 1  represents a substituted or unsubstituted, monovalent fused aromatic heterocyclic group having a ring formed of 8 to 24 atoms; 
 n represents 2, 3, or 4, and the material represented by one of the formulae (16) and (18) comprises a dimer using L 3  as a linking group for n=2, a trimer using L 3  as a linking group for n=3, or a tetramer using L 3  as a linking group for n=4; 
 L 1  represents a single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, monovalent or divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalent or divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with a benzene ring a through a carbon-carbon bond; 
 L 2  represents a single bond, an alkyl or alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl or cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a monovalent or divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, monovalent or divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, monovalent or divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with a benzene ring c through a carbon-carbon bond, provided that, when both X 7  and X 8 , both X 9  and X 10 , or both X 11  and X 12 , represent CR 2 R 3  and both L 1  and L 2  represent substituted or unsubstituted, monovalent or divalent aromatic hydrocarbon groups having a ring formed of 6 to 24 carbon atoms, a case where L 1  and L 2  are simultaneously linked at para positions with respect to a benzene ring b is excluded; 
 when n represents 2, L 3  represents a single bond, an alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having a ring formed of 3 to 20 carbon atoms, a divalent silyl group having 2 to 20 carbon atoms, a substituted or unsubstituted, divalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, divalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond, when n represents 3, L 3  represents a trivalent alkane having 1 to 20 carbon atoms, a substituted or unsubstituted, trivalent cycloalkane having a ring formed of 3 to 20 carbon atoms, a trivalent silyl group having 1 to 20 carbon atoms, a substituted or unsubstituted, trivalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, trivalent aromatic heterocyclic group which has 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond, or when n represents 4, L 3  represents a tetravalent alkane having 1 to 20 carbon atoms, a substituted or unsubstituted, tetravalent cycloalkane having a ring formed of 3 to 20 carbon atoms, a silicon atom, a substituted or unsubstituted, tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted, tetravalent aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring c through a carbon-carbon bond, provided that, when both X 7  and X 8 , both X 9  and X 10 , or both X 11  and X 12 , represent CR 2 R 3  and both L 1  and L 3  represent a substituted or unsubstituted, monovalent, divalent, trivalent, or tetravalent aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, a case where L 1  and L 3  are simultaneously linked at para positions with respect to the benzene ring b is excluded; 
 A l  represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or an aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with L 1  through a carbon-carbon bond, provided that, when L 1  represents an alkyl or alkylene group having 1 to 20 carbon atoms, a case where A 1  represents a hydrogen atom is excluded; 
 A 2  represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or an aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with L 2  through a carbon-carbon bond, provided that, when L 2  represents an alkyl or alkylene group having 1 to 20 carbon atoms, a case where A 2  represents a hydrogen atom is excluded, and, when X 7  and X 8 , X 9  and X 10 , or X 11  and X 12 , each represent O, S, or CR 2 R 3  and both L 1  and L 2  represent single bonds, a case where A 1  and A 2  simultaneously represent hydrogen atoms is excluded; 
 Y 1 , Y 2 , and Y 3  each represent an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having a ring formed of 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having a ring formed of 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group which has a ring formed of 3 to 24 atoms and which is linked with the benzene ring a, b, or c through a carbon-carbon bond, a number of each of Y 1  and Y 3  is 0, 1, 2, or 3, and a number of Y 2  is 0, 1, or 2; and 
 A 1 , A 2 , L 1 , L 2 , and L 3  are each free of any carbonyl group. 
 
     
     
       13. The organic electroluminescence device according to  claim 12 , wherein the material for an organic electroluminescence device in the light emitting layer is represented by any one of formulae (19) to (22): 
       
         
           
           
               
               
           
         
       
       wherein n, L 1 , L 2 , L 3 , A l , A 2 , Y 1 , Y 2 , and Y 3  are as defined in  claim 12 .